Visualizing the Product of a Formal Cycloaddition of 7,7,8,8‐Tetracyano‐p‐quinodimethane (TCNQ) to an Acetylene‐Appended Porphyrin by Scanning Tunneling Microscopy on Au(111)

On‐Surface Reactions

“…Similarly, Diaz Arado et al have shown an oligomerization approach on Au(111), where the azide and the alkyne were present in the same molecule 94. Furthermore, the formal [2+2] cycloaddition between an alkyne‐substituted porphyrin and 7,7,8,8‐tetracyano‐ p ‐quinodimethane (TCNQ) has been shown by Fesser et al95 Table 1 provides an overview of successfully conducted on‐surface reactions carried out in an ultra‐high vacuum.…”

Controlling the Dimensionality and Structure of Supramolecular Porphyrin Assemblies by their Functional Substituents: Dimers, Chains, and Close‐Packed 2D Assemblies

“…The software WSxM was used for data processing . [26] The synthesis of the porphyrin has been described elsewhere 23…”

“…The system presented herein deals with the control of dimensionality of molecular assemblies by the complex interplay of short and long‐range attractive and repulsive interactions. Herein, we report a low‐temperature scanning tunneling microscopy (STM) investigation on the self‐assembly process of a zinc(II) porphyrin (Figure 1 a) on Ag(111) 23. The important feature of this molecule, in the context of its self‐assembly, is the “tail” appended at one meso ‐position of the porphyrin core, which consists of a phenylene spacer, an acetylene and a N,N‐ dimethylanilino (DMA) moiety.…”

“…The molecules were deposited on an atomically clean Ag(111) surface under ultrahigh vacuum (UHV) conditions and were investigated by STM to check their conformational and self‐assembly behavior, aiming for a later co‐deposition of an electron acceptor, possibly reacting covalently with the electron‐rich acetylene integrated in the molecule’s tail. Such a covalent reaction with tetracyanoquinodimethane (TCNQ) molecules on Au(111) has been recently reported 23…”

Cyano‐Functionalized Triarylamines on Coinage Metal Surfaces: Interplay of Intermolecular and Molecule–Substrate Interactions

“…[30] The peak at 399.4 eV can be assignedt ot he nitrogen atom of the cyano group, and its binding energy is comparable to those reported for other cyano-substituted molecules. [31,32] The peak slightly above 401 eV can be assigned to the central Na tom of the triphenylamine unit (Scheme 1). The area ratio of the two N1 sp eaks (central N/cyano N) is 1:2.8 on Au(111)a nd 1:3o n Cu(111), which is close to the theoretical value of 1:3.…”